Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation
The installation of azoles via C–H/N–H cross-coupling is significantly underdeveloped, particularly in benzylic C–H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C‒H bonds e...
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| Veröffentlicht in: | Science China. Chemistry 2021-05, Vol.64 (5), p.800-807 |
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| container_title | Science China. Chemistry |
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| creator | Ruan, Zhixiong Huang, Zhixing Xu, Zhongnan Zeng, Shaogao Feng, Pengju Sun, Ping-Hua |
| description | The installation of azoles
via
C–H/N–H cross-coupling is significantly underdeveloped, particularly in benzylic C–H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C‒H bonds enabled by electrooxidation is described, which proceeds in an undivided cell under mild, catalyst- and chemical-oxidant-free reaction conditions. The strategy empowers the C‒H azolation on primary, secondary, and even challenging tertiary benzylic positions selectively. The remarkable synthetic utility of our approach is highlighted by its easy scalability without overoxidation of products and ample scope with valuable functional groups. The approach can be directly used to install benzyl and azole motifs on highly functionalized drug molecules. |
| doi_str_mv | 10.1007/s11426-020-9938-9 |
| format | Article |
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via
C–H/N–H cross-coupling is significantly underdeveloped, particularly in benzylic C–H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C‒H bonds enabled by electrooxidation is described, which proceeds in an undivided cell under mild, catalyst- and chemical-oxidant-free reaction conditions. The strategy empowers the C‒H azolation on primary, secondary, and even challenging tertiary benzylic positions selectively. The remarkable synthetic utility of our approach is highlighted by its easy scalability without overoxidation of products and ample scope with valuable functional groups. The approach can be directly used to install benzyl and azole motifs on highly functionalized drug molecules.</description><identifier>ISSN: 1674-7291</identifier><identifier>EISSN: 1869-1870</identifier><identifier>DOI: 10.1007/s11426-020-9938-9</identifier><language>eng</language><publisher>Beijing: Science China Press</publisher><subject>Catalysis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Cross coupling ; Electrolytes ; Functional groups ; Heterocyclic compounds ; Oxidizing agents ; Solvents</subject><ispartof>Science China. Chemistry, 2021-05, Vol.64 (5), p.800-807</ispartof><rights>Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2021</rights><rights>Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-97aac3695b7ed2f6c44817e0b0cbc148c2508e4dbecd6832c57288c9b44a3a523</citedby><cites>FETCH-LOGICAL-c316t-97aac3695b7ed2f6c44817e0b0cbc148c2508e4dbecd6832c57288c9b44a3a523</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11426-020-9938-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2918611237?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,776,780,21368,27903,27904,33723,41467,42536,43784,51297</link.rule.ids></links><search><creatorcontrib>Ruan, Zhixiong</creatorcontrib><creatorcontrib>Huang, Zhixing</creatorcontrib><creatorcontrib>Xu, Zhongnan</creatorcontrib><creatorcontrib>Zeng, Shaogao</creatorcontrib><creatorcontrib>Feng, Pengju</creatorcontrib><creatorcontrib>Sun, Ping-Hua</creatorcontrib><title>Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation</title><title>Science China. Chemistry</title><addtitle>Sci. China Chem</addtitle><description>The installation of azoles
via
C–H/N–H cross-coupling is significantly underdeveloped, particularly in benzylic C–H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C‒H bonds enabled by electrooxidation is described, which proceeds in an undivided cell under mild, catalyst- and chemical-oxidant-free reaction conditions. The strategy empowers the C‒H azolation on primary, secondary, and even challenging tertiary benzylic positions selectively. The remarkable synthetic utility of our approach is highlighted by its easy scalability without overoxidation of products and ample scope with valuable functional groups. The approach can be directly used to install benzyl and azole motifs on highly functionalized drug molecules.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Cross coupling</subject><subject>Electrolytes</subject><subject>Functional groups</subject><subject>Heterocyclic compounds</subject><subject>Oxidizing agents</subject><subject>Solvents</subject><issn>1674-7291</issn><issn>1869-1870</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNp1kM1KAzEQx4MoWGofwFvAczRfm4-jFLXCghc9hySbLVvWTU22YHvyGXxEn8TUFTw5l5nD_zfD_AC4JPiaYCxvMiGcCoQpRlozhfQJmBElNCJK4tMyC8mRpJqcg0XOG1yKMUxlNQOr2o4B5dGuA7SH2NuxiwOMLXRhOOz7zsPl18fnCro4NBmGwbo-NNDtYeiDH1OM713zw1yAs9b2OSx--xy83N89L1eofnp4XN7WyDMiRqSltZ4JXTkZGtoKz7kiMmCHvfOEK08rrAJvXPCNUIz6SlKlvHacW2Yryubgatq7TfFtF_JoNnGXhnLSlAeVIIQyWVJkSvkUc06hNdvUvdq0NwSbozMzOTPFmTk6M7owdGJyyQ7rkP42_w99A6qSbwI</recordid><startdate>20210501</startdate><enddate>20210501</enddate><creator>Ruan, Zhixiong</creator><creator>Huang, Zhixing</creator><creator>Xu, Zhongnan</creator><creator>Zeng, Shaogao</creator><creator>Feng, Pengju</creator><creator>Sun, Ping-Hua</creator><general>Science China Press</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FG</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>M2P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>20210501</creationdate><title>Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation</title><author>Ruan, Zhixiong ; Huang, Zhixing ; Xu, Zhongnan ; Zeng, Shaogao ; Feng, Pengju ; Sun, Ping-Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-97aac3695b7ed2f6c44817e0b0cbc148c2508e4dbecd6832c57288c9b44a3a523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Cross coupling</topic><topic>Electrolytes</topic><topic>Functional groups</topic><topic>Heterocyclic compounds</topic><topic>Oxidizing agents</topic><topic>Solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ruan, Zhixiong</creatorcontrib><creatorcontrib>Huang, Zhixing</creatorcontrib><creatorcontrib>Xu, Zhongnan</creatorcontrib><creatorcontrib>Zeng, Shaogao</creatorcontrib><creatorcontrib>Feng, Pengju</creatorcontrib><creatorcontrib>Sun, Ping-Hua</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><jtitle>Science China. Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ruan, Zhixiong</au><au>Huang, Zhixing</au><au>Xu, Zhongnan</au><au>Zeng, Shaogao</au><au>Feng, Pengju</au><au>Sun, Ping-Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation</atitle><jtitle>Science China. Chemistry</jtitle><stitle>Sci. China Chem</stitle><date>2021-05-01</date><risdate>2021</risdate><volume>64</volume><issue>5</issue><spage>800</spage><epage>807</epage><pages>800-807</pages><issn>1674-7291</issn><eissn>1869-1870</eissn><abstract>The installation of azoles
via
C–H/N–H cross-coupling is significantly underdeveloped, particularly in benzylic C–H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C‒H bonds enabled by electrooxidation is described, which proceeds in an undivided cell under mild, catalyst- and chemical-oxidant-free reaction conditions. The strategy empowers the C‒H azolation on primary, secondary, and even challenging tertiary benzylic positions selectively. The remarkable synthetic utility of our approach is highlighted by its easy scalability without overoxidation of products and ample scope with valuable functional groups. The approach can be directly used to install benzyl and azole motifs on highly functionalized drug molecules.</abstract><cop>Beijing</cop><pub>Science China Press</pub><doi>10.1007/s11426-020-9938-9</doi><tpages>8</tpages></addata></record> |
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| subjects | Catalysis Chemistry Chemistry and Materials Science Chemistry/Food Science Cross coupling Electrolytes Functional groups Heterocyclic compounds Oxidizing agents Solvents |
| title | Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation |
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